ethyl (R)-5-bromo-3-(1-methylethyl)pentanoate | 61898-60-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (R)-5-bromo-3-(1-methylethyl)pentanoate
• 英文别名: Pentanoic acid, 3-(2-bromoethyl)-4-methyl-, ethyl ester, (S)-；ethyl (3S)-3-(2-bromoethyl)-4-methylpentanoate
• CAS: 61898-60-0
• 化学式: C₁₀H₁₉BrO₂
• 分子量: 251.164
• InChiKey: XCXVFSTWZZFOQT-SECBINFHSA-N

物化性质

• 沸点：
  256.3±23.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl (R)-5-bromo-3-(1-methylethyl)pentanoate 在 四氯化钛 、 二异丁基氢化铝 、 三乙胺 、 sodium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙二醇二甲醚 、 二氯甲烷 、 丙酮 为溶剂， 生成
  参考文献：
  名称：

  Bridgehead Oxiranyl Sesquiterpenoids. Asymmetric Total Synthesis of (−)-Salsolene Oxide

  摘要：

  DOI：

  10.1021/ja964221+
• 作为产物：
  描述：

  乙醇 、 (R)-4-异丙基四氢-2H-吡喃-2-酮 在 氢溴酸 作用下， 反应 12.0h， 以93%的产率得到ethyl (R)-5-bromo-3-(1-methylethyl)pentanoate
  参考文献：
  名称：

  Regioselective conversion of cycloalkanones to vinyl bromides with 1,2-functionality transposition. A general stratagem

  摘要：

  Cyclic beta-keto esters, available by regioselective acylation of cycloalkanone enolates, are rapidly transformed to alpha,beta-unsaturated acids. This functionality transposition allows the derived 3-hydroxy-4-methylthiazole-2-(3H)-thione derivatives to serve as precursors to synthetically useful vinyl bromides. The process involves heating the hydroxamate ester with AIBN in bromotrichloromethane solution. Alkylative and ring contractive variants of the methodology are highlighted. The short sequence makes available precursors to vinyl anions that are not otherwise conveniently accessible.

  DOI：

  10.1021/jo00021a044

文献信息

• Utilization of the Phenylthio Substituent as a Multipurpose Synthetic Tool. Direct Application to the Enantioselective Construction of (−)-Salsolene Oxide
  作者：Leo A. Paquette、Li-Qiang Sun、Timothy J. N. Watson、Dirk Friedrich、Brett T. Freeman

  DOI：10.1021/jo971244d

  日期：1997.11.1

  Vinyllithium addition to this intermediate proceeds in that stereocontrolled fashion which enables oxy-Cope rearrangement to operate readily under conditions of kinetic control. After hydride reduction, the desulfurization of 16 proceeds with inversion of bridgehead olefin geometry to deliver 17. This access route to the thermodynamically more stable geometric arrangement permits direct entry to 1. Attention

  在结构上空前的倍半萜烯（-）-s烯氧化物（1）是由（R）-（-）-香芹酮以对映选择性的方式合成的。苯硫基取代的乙烯基乙烯酮4的生成，随后是分子内环化为官能化的环丁酮9。向该中间体中添加乙烯基锂的立体控制方式得以进行，这使得氧-Cope重排能够在动力学控制条件下容易地进行。氢化物还原后，16脱硫继续进行，桥头烯烃的几何构型被转化为17。这种进入热力学更稳定的几何构型的通路允许直接进入1。特别注意苯硫基发挥的关键三重功能组一开始就介绍了。
• Regioselective conversion of cycloalkanones to vinyl bromides with 1,2-functionality transposition. A general stratagem
  作者：Leo A. Paquette、Karl Dahnke、Julien Doyon、Wei He、Kenetha Wyant、Dirk Friedrich

  DOI：10.1021/jo00021a044

  日期：1991.10

  Cyclic beta-keto esters, available by regioselective acylation of cycloalkanone enolates, are rapidly transformed to alpha,beta-unsaturated acids. This functionality transposition allows the derived 3-hydroxy-4-methylthiazole-2-(3H)-thione derivatives to serve as precursors to synthetically useful vinyl bromides. The process involves heating the hydroxamate ester with AIBN in bromotrichloromethane solution. Alkylative and ring contractive variants of the methodology are highlighted. The short sequence makes available precursors to vinyl anions that are not otherwise conveniently accessible.
• Bridgehead Oxiranyl Sesquiterpenoids. Asymmetric Total Synthesis of (−)-Salsolene Oxide
  作者：Leo A. Paquette、Li-Qiang Sun、Timothy J. N. Watson、Dirk Friedrich、Brett T. Freeman

  DOI：10.1021/ja964221+

  日期：1997.3.1